"he told me that he was looking for a hole in the clouds as he did not hold a current IFR rating."
If he had told you that he was looking for a hole in the clouds and he had a current IFR rating would you have relaxed?
I am surprised he mentioned that he had not.
This is not an uncommon event in African aviation where typically a bush pilot knows the area and terrain. As you mention the pilot had a reasonable idea of what he was doing.
Recently in Kenya another pilot never found the hole and descended killing all on board.
Job well done to the pilot. Dont get me wrong I understand your concern.